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Did Jack Conway go too far?

A new ad being run by state Attorney General Jack Conway (D) against ophthalmologist Rand Paul (R) in the Kentucky Senate race using several college-era incidents to raise questions about the Republican's character has created a national firestorm.

"Why was Rand Paul a member of a secret society that called the Holy Bible a 'hoax'," asks the ad's narrator. "Why did Rand Paul once tie a woman up, tell her to bow down before a false idol and say his god was 'Aqua Buddha'."

"This is an ad about things he did," said Conway campaign manager John Collins of the allegations in the ad. "He has failed to deny any of these charges."

Paul, for his part, struck back with an ad own his own in which a narrator says he keeps "Christ in his heart" and attacks Conway for bearing "false witness".

Regardless of the veracity of either/both of the charges, the ad amounts to a major gamble for Conway. Down only a handful of points in most public polling, it now seems clear that this ad could make or break the race -- forcing voters to decide whether Paul's college transgressions are fair game in the context of a political race or whether Conway went too far and, in so doing, made himself look like a desperate candidate looking for a Hail Mary political pass.

Recent political history provides a mixed bag when seeking to assess which way this Conway ad will play with voters.

The most obvious comparison to the Paul ad is one that then Sen. Elizabeth Dole (R-N.C.) ran against state Sen. Kay Hagan (D) in the waning days of the 2008 North Carolina Senate race.

Late in October 2008, Dole when she launched what is now commonly known as the "Godless American" ad -- insinuating that Hagan's attendance at a fundraiser sponsored by a leader of the Godless Americans PAC raised questions about her religious beliefs.

Here's that ad:

Hagan, smartly, responded with a commercial of her own accusing Dole of "bearing false witness against fellow Christians." (Sound familiar?)

The race, which was already slipping from Dole, quickly turned into a landslide -- movement largely attributed to the blowback from that ad. Hagan won by a whopping nine points.

And yet, not all ads that go after a candidate's character have had that sort of negative boomerang effect.

The most famous recent example was a commercial run by Sen. Max Baucus (D) in his 2002 race against state Sen. Mike Taylor (R). The ad, which you must watch here, used footage of Taylor applying makeup to another man's face while the narrator detailed the Republican's work at "beauty salon and a hair care school."

It pivoted to attacking Taylor for abusing the student loan program and diverting money to himself." The ad, which also featured an image of Taylor rubbing the man's temples -- closed with the narrator saying: "Mike Taylor...not the way we do business here in Montana."

Taylor dropped out of the race -- in mid-October! -- insisting that the ad crossed the line into character assassination. Bacus won 63 percent to 32 percent.

(It's worth noting that while the North Carolina race was regarded as competitive when Dole aired her ad, Baucus was already a strong favorite when his ad aired.)

So, is the Conway ad more Dole circa 2008 or Baucus circa 2002? Missouri Sen. Claire McCaskill (D) seemed to at least hint that it belonged in the former category, telling "Morning Joe" that the commercial was "very dangerous" and "came close to the line" of what is appropriate in the context of a campaign.

One senior Democratic consultant, however, insisted the verdict is still out. "It's reasonable to wonder whether it's relevant," the source said of the ad. "But presumably they've done their research on that point."

The next few days will be critical in judging whether the ad worked or backfired Conway's campaign is holding its ground and Paul seems to want to have the debate. Stay tuned.